


Roommates

by JackTrades



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Cunnilingus, Dirty Talk, F/M, Filthy, Fingerfucking, Group Sex, M/M, Massage, Plot What Plot/Porn Without Plot, Sex Toys, Strip Tease, Stripping, Voyeurism, Wincest - Freeform
Language: English
Status: Completed
Published: 2015-04-04
Updated: 2015-04-06
Packaged: 2018-03-21 05:49:39
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 10,035
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3680319
Author URL: https://archiveofourown.org/users/JackTrades/pseuds/JackTrades
Summary: <blockquote class="userstuff">
              <p>After a hunt turns out to be a bust, Sam and Dean go out to blow off steam.  They unintentionally end up hooking up with women who are roommates.</p>
            </blockquote>





	1. Dean

**Author's Note:**

> This is my first multi-chapter work. If you're only here for the Wincest it's in chapter 3.

The boys found thought they were tracking a potential ghost or vengeful spirit.  They had checked into a run down motel and began pouring hours of research at the local library; only to find out police had arrested a suspect for the crimes. Thorough double-checking confirmed that the culprit was, in fact, the very much human person in custody. Not all cases are interesting. 

Their room was already paid through the day though. So when everything was wrapped up before ten o’clock at night, Dean naturally suggested that they go to a bar within walking distance, get plastered, and check out in the morning. Under normal circumstances, Sam would be the “rational, responsible one” and talk him out of it. Except that he really was fired up and ready to chase something down – and that energy wasn’t going anywhere on its own.  So, yeah, why the hell not? Go drink until the energy died down, or let the booze do its job and find him another constructive way to get his energy down.  

Luckily for them, the dive bar that they wandered into looked like shit on the outside but was actually comfortable on the inside.  Beats the hell out of hanging out in the motel room that looked like it had hepatitis. Dean went out of his way to go to the side of the bar with the hot female bartender, ordering two beers and two whiskeys.  If they were going to get shit-faced they were going to do it right! Sam got the hint and downed both quickly along with Dean before ordering another round. They grabbed a table in the corner to get a feel for the place.  No pool table, no darts, not even freaking shuffleboard! From what they could gather it was a hybrid bar-restaurant that had bands and DJs on the weekends but was otherwise littered with only regulars during the week. 

Sam was sent up for round three when a hot brunette started chatting with him.  When she leaned over the bar to tell the bartender her order, Sam turned to Dean and they had a silent conversation from across the room.  _Play your cards right and you might get laid, Sammy.  I can find a way to entertain myself._   

The girl next to Sam turned back she was shoving a shot glass in his face.  Dean didn’t need to read lips or anything to know the “Take a shot with me” face. Knowing Sam, he’d find a way to fuck this up if he thought Dean was watching too closely, so Dean took the opportunity to go to the men’s room.  On his way out, he almost ran into Sam. “So she uh….” Stupid, flustered Sammy, “I’m gonna get out of here with her, you ok?” 

Dean couldn’t stop his shit-eating grin if he tried, “Go for it Sammy! See you in the morning.” He made sure to give an exaggerated wink as he sauntered over to the bar to continue his night.  The competitive part of him really wanted to pick someone up, just so Sam didn’t get exclusive bragging rights on this bust of a case.  At any rate, this bar would not be open much longer since it was a weeknight.  He’d have to be efficient. 

He flagged the girl behind the bar.  He'd be lying if he tried to claim his eyes didn't zero in on her ass the second he went to the bar to order round one at the beginning of the night. He caught her checking him out a few times throughout the night.  She wore a tight fitting t-shirt with the bar's logo that didn't quite meet the hem of the short shorts she had on. Even in sneakers, she had a firm, round ass.  Throughout the night, as she would grab the bottle opener from her back right pocket, Dean couldn't stop his eyes from tracking the movement.  Redhead too.  Bonus. That definitely increased the chances of at least fooling around with her... or getting in a knockdown drag out fight with her boyfriend if he tried something. Worth the chance! 

Either the booze made him less adept at covering his ogling or she was a sure thing from when she first saw him, doesn't matter, because the second Sam left with a girl and Dean moved to the bar, she was on him.  He figured out her name was Amy and he was good until she got two rounds of shots for him.  After that second one he coyly raised an eyebrow and asked, "What're you tryin' to get me drunk so you can take advantage of me?" 

The response was a look that left no mystery, but not verbal. He ordered two waters to pound in the half hour that the bar would have before last call, not realizing it had already been called while he was in the bathroom.  He knew from hooking up with bartenders before, you gotta wait until at least last call before you can get them to leave. Especially a girl that hot, no way she'd be so happy to have sex with him that she'd forfeit her tips. Three waters in, and the other staff members divided their money and she was cut loose.  That was still only thirty minutes after his last shot. Plenty of time to walk her to the motel and shake his buzz… until she said she had a car and could takes him to her place instead.  He needed at least ten more minutes than that allowed but he could improvise. They were to the large house she shared with several roommates in no time, and to her bedroom just as quickly. 

Okay, so he drank a lot more than one should before sex.  Sure, he still felt the slight buzz from all the booze earlier but it had faded to a pleasant, fuzzy tingle. Most of his body was busy processing said alcohol when he realized he had a sure thing with the bartender. His brain was ready to go, she was certainly ready too, but his drunk traitor of a dick was moving at the speed of slow to join the party.  He had the beginnings of an erection though, and from unfortunate experience with alcohol hindering his ability to get it up, he knew he could work with this. Hell, he could work with this and she'd be none the wiser if he could help it! 

Deciding on being "gently assertive," he pushed her back onto the bed playfully.  He pulled his shirt and jacket off before leaning down to steal a quick kiss. She was about to pull her shirt off when he stopped her, "Let me." He even threw in one of those panty-melting smiles as he met her eyes. Yeah, he could work with this. He could make her feel good - no, fantastic! - while the blood in his body that wasn't alcohol made its way to south. 

He started at her sneakers, pulling one leg to his chest. He knew from that look that she was giving him that it was a little bit of a turn on for her, being sprawled out on the bed while he remained standing.  It was her bed so he knew he'd have to get those off if he wanted her legs on the bed without protest.  He used his right hand to untie and loosen the laces while his left hand dug into the meaty part of her calf rubbing circles on the overworked muscles.  She let out a more-than-appreciative moan and leaned back to get a better view of what he was doing. 

Once the laces were loose, he pulled off her sock and shoe in one swoop. He turned and placed it at the foot of the bed.  Experience also told him don't leave trip hazards if you plan on making a quick exit. He moved both hands to her foot and started digging his thumbs into the arch of her foot. He didn't plan on spending too much time on this, but he always did get off on making a girl loose, pliant, and relaxed before getting to the good stuff.  It's the noises they make, the unconscious moans and whimpers that tell him he's going to burn himself into their memories.  The impromptu foot massage only last three or four minutes before he gently placed her foot on the bed and picked up the other leg.  Taking the hint, she scooted up onto the bed and leaned back on the pillows.  

Dean dropped her leg for a moment to quickly get rid of his own shoes and socks before kneeling on the bed. He tapped her on the inner thigh to indicate that she should bring her leg up. When she lifted, he grabbed it and brought it to his chest. He repeated the same treatment with this foot before placing small, quick kisses to her ankle and starting to trail up. He got to mid calf when he decided to change course.  His dick was starting to become a little uncomfortable in his jeans (way to get with the program!) but he wanted to drag this out.  If he was being given the opportunity to make this last until the morning, he wasn't going to waste it by jumping into going down on her too soon.  And, selfishly, he wanted to see her beg for it.  She'd definitely do that if he kept to his plan. 

He pushed her legs a little further apart then leaned over her to kiss the part of her stomach that was exposed.  He slid her shirt up as he slowly made his way up her body. She was giggling and squirming slightly.  He pulled back to tease, "You're ticklish?" He figured it out easily enough but she nodded yes to him. "Good to know," he said before he dove back down to continue his path up, intentionally dragging his stubble against her soft, exposed skin. He dragged the backs of his fingernails up her sides just for good measure – god he loved ticklish girls! 

She was clawing at the back of his head and pulling his hair slightly by the time he made it to the underside of her bra.  He leaned back to pull her shirt over her head before licking and nipping along her neck, pushing her one strap down and reaching underneath her to deftly unhook her bra.  He made quick work of discarding her bra and took a leisurely trail down to her right breast.  Palming the left as he worked, he flicked his tongue over her nipple before sucking it gently. She was letting out soft gasps and biting her lip, clearly trying to keep from making too much noise. That won’t do… Dean redoubled his efforts, sucking hard as he purposely tickling her sides as he did it. 

A loud moan rang through the air, but it wasn’t from this room. Keening mixed with what could have been “Oh my god” but who knows? Dean laughed and kept going. 

He stretched up and draped himself over her, leaning most of his weight on his elbows on either side of her head.  The hot press of skin-on-skin caused both of them to sigh as he ran his fingers through her hair and pressed in for a deep kiss. Dean prided himself on being good with his mouth, and kissing was definitely in his Top Three favorite activities. He took his time, enjoying the contrast of pressure and softness before parting his lips to coax hers open. As he deepened the kiss, he shifted his weight and moved his free hand down between them to start shoving her shorts and panties down.  Reluctantly, he pulled back from the kiss when he couldn’t get them past the middle of her thighs.  Leaning back on his haunches, he gently grabbed behind her knees and rolled them toward her chest.  He snatched the material from her legs and tugged the garments off, throwing them to the floor. Afterward, he kept her legs up, kissing behind her knee and purposely dragging his stubble there just to make her squirm.  Satisfied with his progress, he pushed her legs open and started to lean over her again… 

The sound of moaning from the other side of the wall was a little too loud to ignore the second time.  From what Dean could gather, the woman on the other side was either a gifted faker or about to have an orgasm.  “Um – excuse me,” his date said as she playfully nudged him with her foot. 

“Sorry,” he played it off with a naughty eyebrow raise and a smile. “Sounds we’re going to have to put on a show for your roommate whenever she’s done.” He leaned back in, pressing his mouth to hers in an unhurried kiss, trailing a hand down her leg and encouraging her to wrap it around his hip.  He slid a hand between her legs to – finally – start teasing her clit.  His buildup was worth it, she was already soaked, and he’d happily have her strung out on sex in no time.  Gentle pressure, small circles, with the occasional wrist flick: he had his technique down. She was moaning into his mouth, one hand digging into his bicep and the other alternating for purchase between his back and his ass.  He pulled away from her mouth just enough to see her face while she panted his name, she was close, he could draw it out and keep her on edge – but he was in a giving mood tonight.  He felt her muscles lock up as her eyes rolled back, gushing on his hand.  “Gorgeous,” he whispered into her ear before kissing a trail down her chest and stomach.  He was set to lick her open, keeping eye contact with her as he sucked his fingers into his mouth. 

That’s when he heard the girl next door again, and there was no mistaking what he heard: “Sam! Sam!” mixed with a high-pitched scream.  

He knew better, but the curiosity would have killed him, there’s no way it was his brother in the other room. No way they managed to go home with two girls that lived together. Not with all the girls in the entire city. So Dean perked up and yelled loud enough to shout through the wall, “SAMMY? Is that you?” The redhead underneath him laughing as he asked. 

“DEAN?!” 

“Oh shut up,” Dean laughed as he buried his face into the girl’s hip to muffle the worst of it. 

“What?” she asked. 

He kept laughing for a second before answering, “Out of all the girls to hook up with, apparently my brother ended up coming home with one of your roommates.” He was still laughing when he started licking the inside of her thigh moving towards her pussy. 

A loud banging on the door interrupted that exchange, “DEAN! Hallway. Now.”

 

Dean chuckled to himself and gave her one quick peck on the inside of her thigh, “Be right back.” He adjusted himself and made sure his jeans were on before going to see what Sam was going to bitch about…

 

 


	2. Sam

**Summary for the Chapter:**

> Sam's version of what happened

**Notes for the Chapter:**

> Just in case you were not familiar with the song I reference in this chapter here's the link on YouTube: https://www.youtube.com/watch?v=BGtjc8Qgp6g
> 
> I know it'd drive me crazy if there was a song reference I wasn't familiar with that would take me out of the moment.

If Stanford taught him anything, it was how to maybe, possibly, identify when a girl looks at him like she has definitively made the decision to fuck him.  Under any other circumstance he would have brushed her off and waited for Dean to be too drunk to contain or leave with a girl.  So maybe Dean’s teasing was getting to him: “You know, Sammy, if you got laid it would probably help with your concentration,” “Picking your water bottle label is a sign of sexual frustration,” “Ugh, why don’t you just have sex with that book already – not like you’re getting any from a girl anytime soon” … So, yeah, maybe Dean was getting to him in a way only a sibling and almost zero privacy can. 

Pacing Dean while drinking was always a dangerous endeavor. Not because he couldn’t handle his booze, but because they were hardwired to always have an eye out for something or someone getting the jump on them.  His empty glass hadn’t even hit the table when Dean insisted, “Your round!” Sam’s own buzz was pleasant enough that he couldn’t muster a bitch-face and he went to the bar to try to squeeze in and get one of the bartenders’ attentions.  

As he got closer, that’s when he saw that look on the brunette near the corner of the bar.  She got closer to him, crowding him slightly and asked, “You need a drink? If you’re not a regular, they take a while to get to you sometimes.  I’ll get them for you. I’m Tara, by the way.” 

“Sam, thanks.”

 “So Sam, what are you drinking?” 

“My brother and I are switching between beer and whiskey,” he said gesturing toward Dean at the table.  That’s when he could clearly read Dean’s expression of ‘fuck this up and I will make your life miserable’ from his vantage point. 

“On a Wednesday? I like your style,” she said, sliding a hand onto his forearm.  “Do a shot with me – it’ll be fun! I promise!” 

“On a Wednesday?” Sam couldn’t stop the sassy reply before it came out of his mouth.  Luckily for him, she seemed to like that answer.  She flagged the redheaded bartender and ordered two of… something. It didn’t look strong, more sugar and color than actual alcohol content.  He was expecting one, not two, as a second glass appeared in front of his face between her slender fingers. 

“I can tell you’re not from around here, so where are you staying tonight?” Can’t blame the girl for forgoing subtly. 

“We’re at the Pine Lodge Motel up the street –“

 “Ugh! Gross – do they still have roaches the size of beer cans there?! I’m sorry – I went there once, when I first moved to town as place to hook up and I swear I think I burned what I wore there because it was so nasty.” 

“I have stayed at a lot of motels, and that one is…. Special,” she laughed, “But we needed to get a place to stay just for the night and, hey, we’re out here instead of hanging out in the room –“ 

“So then you’re not really in a rush to go back to that motel?”

 “Not if you’ve got a better offer,” did he really just say that? God, that’s the shit Dean would say that made him roll his eyes in amusement. 

She raised an eyebrow and signaled the bartender to close her tab.  The perky redhead was even kind enough to bring Sam his check too.  He just needed to let Dean know he was leaving, where was Dean anyway? “I’m just going to hit the bathroom, why don’t you get us a cab? I’ll pay.” 

He nearly slammed into Dean as he went to enter the bathroom. “So she uh….” Sam gestured toward the door and the girl waiting, “I’m gonna get out of here with her, you ok?” 

“Go for it Sammy! See you in the morning,” Dean gave an obnoxious wink. He fumbled in his pockets shoving a condom in Sam’s hand before bellying up to the bar.  As much as Sam wanted to kill him, he was silently grateful because his night would have gone bad pretty fast without it.

 Sam met Tara at the door and got into the waiting taxi.  She gave her address to the driver and turned to Sam, “It’s like a four minute drive without tra—” her sentence was cut off as Sam pulled her into a rough, crushing kiss.  Four minutes? He could work with that.  If she was shocked, she got with the program quickly.  She wrapped one hand in his hair, pulling slightly for leverage, and the other rubbed roughly over his denim clad crotch. 

“Hey!” the driver yelled, “No making out in the car!” 

Sam chuckled into the kiss and reluctantly pulled away from her.  He let his hand slip under her skirt and teasingly, promisingly, rub over her panties.  She bit her lip hard to stifle a moan. 

“OK, we’re here.  That’ll be $14.75 plus tip,” the driver pulled up in front of a fairly large house. Sam threw him twenty bucks with a muttered, “Keep the change,” as he tried to casually, but efficiently get back to what he started once he was inside the house. 

She grabbed her purse and was digging for her keys as she explained, “I’ve got three roommates but they don’t care about… overnight guests.” She was fumbling with the lock as she continued, Sam took a minute to appreciate how tight and short her skirt was while she was slightly bent over to access the lock.

Once she had the door unlocked she grabbed him by the arm and dragged him up the stairs immediate next to the door, she didn’t miss a beat or slow down until she had him in a room at the end of the hallway.  She barely had the time to throw her bag and keys on the nightstand and close the door when Sam was on her.  Alcohol always made him more bold and controlling about these situations.  He grabbed her by the hips and hoisted her up against the door – hey, why should he always have to bend over for girls? She didn’t weigh much and he wasn’t actually supporting all of her weight.  She wrapped her legs around his hips, her skirt hiking up to her waist in the process. Her hands alternated between running through his hair and grabbing at his arms and back – clearly he’d made the right move because she was really turned on by being manhandled against a door, even if he wasn’t being particularly aggressive in the way he was kissing her right now.  After ten or fifteen minutes, his arms did start to get tired though.  So he made sure he had a good grip before hoisting her and moving the six or so steps to the king size bed in the room. He put her down gentle and leaned back to stand and get to work on his own clothes.

That’s when he got a look at the room.  There was actually almost no furniture in the room except the bed and the nightstand.  He must have looked confused because she piped up, “Yeah, yeah, I know it’s kind of a ridiculous size bed for this room.  My last place had a bigger room with high ceilings, the bed was proportional then!” 

“Trust me, you won’t hear me complaining,” he laughed to lighten the mood. 

He went to pull his jacket off when she grabbed his hands.  This girl clearly knows how to have a good time, so hopefully the next thing out of her mouth wasn’t going to be a deal breaker, that’s always the worst. “Not so fast, I want you to do it slowly,” she almost purred at the end of that.  

Sam raised an eyebrow.  It wouldn’t be the first time that was requested, but it always made him a little self-conscious. The idea of someone sitting back, studying his every move, having the time to spot every healed salt round, bite, and slash scar on his body, while he was on display just made him a little uneasy. He was quickly assessing this; he had to say something quickly before it got awkward. “Music? I can’t really do this without that…” Good save, bought him more time to silently panic while he decided if he was actually going to do it. 

She scooted over to her bag and started digging through it.  After a few seconds, she produced an iPod from the bag and clipped it onto the top of the alarm on the nightstand. “You have a preference?” she was definitely baiting him now. 

“Lady’s choice,” he gave an exaggerated gesture with his arms open to her, “One request though…” She raised an eyebrow and he continued, “Can I just take my shoes off now? I mean, really, there’s no sexy way for me to do get them off.” 

Her laugh in response was genuine.  Not in a laughing-at-him way, but in an I-never-thought-about-that way. “Oh my God, you’re adorable!” As he sat down on the edge of the bed, she pulled him into a deep kiss. Probably to drive home the point that she wasn’t laughing at him, just his observation.  This made getting his shoes off infinitely more difficult, but maybe he could distract her from this idea if he tried hard enough. He shed his jacket and finally managed to get his shoes off before getting her to lie down, definitely more tongue than before and Sam wasn’t complaining about that.  He wasn’t expecting it when she pulled back, “Don’t think you’re getting out of it that easily, mister.” 

He responded with an exaggerated pout, “But we were getting to the good part – ” 

“Yeah. The part where you dance for me,” she grinned as she shimmied back up the bed and started scanning through her song selection.  Sam stood and walked to the side of the bed.  He could do this.  In his experience, a little bit of a show could result is an absolutely wild night. Win-win really. And with their last few months of hunts, Sam had been getting more exercise (er, running for his life) in than usual… he had a healthy amount of pride about how his body looked. So fine, he could make this enjoyable for her.  She seemed satisfied with her choice as she turned on the music and propped herself up on the bed to watch him.  “Black Velvet” started playing out of the speaker and Sam couldn’t stop the full body laugh from coming from him, even if he wasn’t tipsy.  It wasn’t what he was expecting.  The song is like countless others that Dean would sing off key in the car, hell, Dean had just been singing Heart in the motel room right before they left for the bar.  Certainly not the rap or R&B song he was expecting.  

Sam gathered himself, “Sorry.  It’s just not what I was expecting – it’s good though!” He took a deep breath and closed his eyes, swaying slightly, taking a moment to gather his thoughts. He’d heard the song countless times, so he knew how much time he had to work with.  He locked eyes with her and began lip-syncing the lyrics of the song at the first chorus, unbuttoning the left sleeve of his flannel shirt and rolling it up to the elbow, then repeating the action on his right sleeve. He made sure that he was swaying his hips and giving the most intense “fuck me eyes” that he could give while still performing a task that required is coordination.  He purposely ran his hands through his hair and started unsnapping the buttons of his flannel shirt one at a time; he had a tight fitting grey t-shirt on underneath.  Pulling one arm free, he got the shirt off his other arm then wadded it up and tossed it at the girl.  He turned slightly and caught a glimpse of the mirror over his shoulder and decided to work with it.  He’d been complimented on his ass enough times to know he should be letting her get a better view of it.  Turning around to have his back to her, he continued but looked at her in the mirror as he slid his hands to the hem of his shirt and slowly moved it up. He could see her moving to the edge of the bed in the mirror, letting her legs hang off the side as she sat. He pulled his shirt off then turned to her and tried to hide his blush when she gasped as she looked at his abs. 

He reached for the hem of her shirt and pulled it off her, and was pleasantly surprised that she wasn’t wearing a bra.  He pushed her legs together and bracketed them with his own, then reaching under her to pull her skirt and panties off.  He pulled her a little closer to the edge of the bed and spread her legs as wide as the comfortably could go.  Stepping back, he went back to moving his hips as he went for his belt.  Taking the hint, she leaned back slightly and began slowly stroking circles over her clit as she watched him.  Once the buckle was open, he decided to not screw around with removing it from his jeans. Instead he went for his fly and popped the top button.  He had to bite his lip to stifle his relieved groan when he slid the zipper down, finally letting up some pressure on his cock that he had been ignoring. 

He let his jeans drop and stepped out of them before following them to the floor as he got on his knees between her legs.  He took her wrist in his hand and guided it to his mouth so he could suck her fingers.  When he was done tasting her on her fingers, he dove down between her legs to get a direct taste. He gripped her thighs and lifted her a little bit so that her ass wasn’t on the bed anymore, he wanted better access to her. After a quick flick of his tongue over her clit, he licked a long stripe from her ass back to her clit, eliciting a loud moan from her as she buried a hand in his hair.  Taking this as a cue, he dared to flick his tongue over her asshole a few more times.  She practically arched in half. “Oh my god!” she screamed as her fists balled into the comforter on the bed.  He always was a fan of playing with a girl’s ass, probably because they reacted so well and it didn’t always get the attention it rightfully deserved.  He put her down and encouraged her to roll over as he climbed onto the bed.  He got her on the elbows and knees so he could go back to eating her out in earnest, slipping a finger into her pussy as he worked her ass. She was practically howling when he pulled back.  “Shit, do you have lube?" he was going to press and see if she went with it. 

"Yeah, top drawer," she gestured to the nightstand on the right side of the bed.  He opened the drawer to fish around and felt a few bottles, he sat up to look more carefully: two or three bottles of perfume, a box of safety pins, condoms - "Well, hello!" he shouldn't be so proud to find her vibrator.

"Oh geez, sorry, I know that I have lube in here..." producing some sort of fancy clear bottle with a black pump, "Here you go." She handed him the bottle and attempted to take the vibrator from him.

"No no, I found it -" he wasn’t letting her get it from him that easily. 

"So it's yours now?" She teased. 

"So I get to use it on you!" She blushed, actually outright blushed. Now Sam had seen everything, this girl had been a sex fiend since she first saw him but was now getting flustered at his suggestion. "What? Are you worried I'll use it on you better than you do?" He couldn't help his wicked, predatory grin. 

She snapped up, "No! It's just... I never had anyone else do it to me before," she was clearly open to it. She just needed that last nudge of encouragement.

"I'll make you feel so good, I promise," he nipped her earlobe as he spoke. "Come on, please." She shuddered, outright shuddered, at that.  Sam knew what a sincere, sex-laced 'please' could do to a woman.  

He could feel her frantic nodding before she spoke, "Okay, yeah."

The vibrator was one he'd seen before, and fortunately for him (and her) he knew how to use it.  It was a rabbit vibrator, or some other cutesy one like it.  Bright pink, and of course, a weird smiley face on it near the flared head.  He wasn't going to focus on that, instead he rearranged her so she was on her back with her head at the top of the bed near the pillows.  He encouraged her to lift her hips up so he could shove a couple of pillows under her butt and lower back. Then he settled between her spread legs, taking a few seconds to appreciate the view: pale, smooth skin, small but perky breasts leaning slightly towards her face from the angle of her body, and inner thighs glistening with slick.  Her pussy was enticing, fluttering slightly with her ragged breathing and leaking with excitement.  Maybe he could have gotten away without the lube after all. But he was still on a mission. He took a slight detour to teasingly run a finger against the rim of her entrance, before plunging two fingers in again.  She arched her back and threw her head back with a loud moan as he gave slow, shallow strokes, scissoring his fingers slightly.  Thank god they came here, anything that loud at the motel would have gotten him a warning call from the front desk. “I thought you were gonna use that,” she panted as she gestured toward the vibrator that was sitting on the bed.  

“Patience…” he chided as he purposely pressed hard on the sensitive bundle of nerves inside her walls.  While he continued fingering, he used his free hand to pump some lube onto the vibrator and slick it up.  He pulled his fingers out to hold her lips open as he slid the vibrator inside her, he moaned at the sight of the object plunging into her.  When he got it to the point that the clit stimulator was close to its target, he purposely pulled it back out so only the head was in and switched hands.  He started a slow slide in and out as he slicked the fingers of his other hand and circled her asshole with one.  He fumbled with the controls at the base of the toy, trying to remember if it was “vibrate left, rotate right” or the other way around, and decided to just turn both on.  She nearly screamed as she arched off the bed, he’d have to make the decision quickly if he was going to keep her on edge or just make her come over and over.  He decided on the latter as he pushed one lube slicked finger into her ass, groaning at how he could feel the toy working her as he spread the lube.  He turned up the speed on the toy as he continued thrusting it into her and added a second finger to her ass, scissoring them to start opening her up.  It as all too much when he decided to hit the reverse button on the vibrator, it probably didn’t even take a full circling of the head and beads in it to have her gushing hard and screaming, “Sam! Sam!” through her orgasm. 

He turned off the toy, being merciful instead of relentless, and pulled it out of her, “You look gorgeous like this…” 

And his moment was interrupted when he heard a voice through the wall, “Sammy? Is that you?” followed by a distinct bark of laughter that could only be one damn person… 

“DEAN?” no way. There is no way that of all the women Dean could have picked up in the short time since he left the bar, it happened to be one that lives with the girl he’s currently trying to have sex with. The muffled laugh, distinctly Dean’s, and that of a girl with him were too distracting.  No way.  No fucking way is he going to be able to get laid with Dean there. He huffed in annoyance and got up off the bed, “Be right back, apparently your roommate picked up my brother after we left.  I just need to talk to him real quick.” 

He shoved his jeans on and went to the hallway to pound on the door, “DEAN! Hallway. Now.”


	3. Conflict Resolution

**Summary for the Chapter:**

> Conclusion to Sam and Dean hooking up

**Notes for the Chapter:**

> I may have taken this too far.

Dean couldn’t contain the swagger in his step as he left the bedroom to meet Sam in the hallway.  He was grinning ear to ear as he looked at Sam, “What’s up, Sammy?” 

“Leave.  I can’t enjoy myself if you’re going to be here listening the whole time for shit you’re gonna make fun of me for later!” 

“Sorry, I’m a little too busy having fun myself. But now that you mention it, maybe I’ll just wait until you’re done so I have long term entertainment….”

* * *

 

Tara was in the room partially listening to the conversation in the hall, but was preoccupied with grabbing her cell phone from her purse.  Once she got it she sent a text to Amy. 

_Tara: OMG! Those two are brothers!_

_Amy: I know! This will still work though_

_Amy: I told you they looked totally fuckable when they came in_

_Tara: Ugh.. Sounds like they’re gonna argue for a while_

_Amy: I’ve got a plan if they don’t wrap this shit up quick_

* * *

“Dean, you can’t be fucking serious! After all the shit you give me about getting laid, you’d be this much of a dick about it!” 

“Not my fault you can’t get it up!” 

“I can get it up, but I can’t concentrate and keep it up if you’re snickering in the room next to me.  Just find another place to go – I was here first!” 

“I’m not the one with the problem, princess! Not like we haven’t heard each other have sex before.” 

“We’re not teenagers trying to make due and split one room anymore!” 

Their argument was interrupted when Amy walked out of her room, naked as Dean had left her.  A naked woman always could put a hiccup in their bickering. “I don’t know how long you two are gonna be, but I’ll be playing with Tara until you straighten this out,” she made sure to throw a sultry look over her shoulder as she walked into the other room and closed the door. 

“I’m definitely not leaving now Sammy! I was just gonna bust your balls a little bit but that,” Dean pointed to the door, “THAT is a game changer.  If a threesome is on the table, you need to leave.” 

“And why do you: 1, assume that it’s a threesome, and 2, assume YOU get to go in there!” Dean thought he’d already seen every shade of bitch-face Sam could make, but apparently the ‘you’re not stealing my threesome opportunity’ situation had its own unique bitch-face.  Dean couldn’t stop laughing at the idea of it. “It’s not funny!” 

“Yes it is,” Dean managed to get out between laughs, “Jesus, why are you so serious? It’s sex.  It’s supposed to be fun.  Clearly those two want to have fun and I, for one, want to give that to them.” 

He started towards the door when Sam stopped him with an extended arm to the chest, “I am going back in too, so are you going to be an asshole about this or not?” 

Dean’s grin was back, “Are you trying to negotiate terms?” 

“You stay with the girl you came here with, I stay with the girl I came here with.  Unless they change the terms that’s what we’re doing,” Sam reasoned. 

“I’m game if you are,” Dean replied. Sam lowered his arm and nodded in assent.  They had been in close quarters their whole lives, this particular situation never presented itself but they could deal… or at least Sam hoped they could deal. 

Dean opened the door and both walked in. The girls were lying on the bed with their heads on the pillows, Tara on her back and Amy on her side facing the door.  Amy grinned and spoke up, “I knew it was a good idea to wait instead of starting without you…” Tara was playing with Amy’s hair.  Both girls looking at the two of them like a predator looks at its prey. 

“So how do you want to do this?” Sam asked. It came off more shy than he wanted it to.  For his part, Dean actually kept his mouth shut.  Sam noticed the ever-so-slight fidgeting he was doing and it dawned on him, Dean was _nervous_.  Well, that’s a first. 

The girls paused; they looked at each other and were clearly having a silent conversation.  Tara rolled on her side and Amy leaned over, idly tracing a finger up and down her arm.  Both men couldn’t stop staring and following the movement.  Tara spoke first, “We were talking before you came back in,” Amy nodded. “We both think you’re really hot, but now we found out you’re brothers!” Amy interjected, “Super hot…” Tara continued, “We wanna see you two fool around with each other…”

 _Nope._ That was the thought that ran through Dean’s head.  He was ready to say as much when Sam acted.  Rather than echo his sentiments, Sam threw an arm around Dean’s shoulder and ghosted the other hand across Dean’s chest.  Before Dean even time to process what was going on, Sam leaned in and licked a broad stripe from his collarbone to his jaw then jerked Dean’s face toward him to catch his full lower lip between his teeth pulling back slightly before letting it go.  He couldn’t help the groan that escaped his lips, Sam, that fucker, knew from many long, detailed tales of Dean’s sexual escapades that doing that was a huge turn on for Dean.  And ‘turn on’ and ‘Sam’ shouldn’t even be in the same sentence.  An ‘ _Oh shit…’_ registered in Dean’s ears but he couldn’t decipher which girl said it, his blood was pounding in his ears as his brain helplessly tried to catch up with the proceedings.  Sam pulled back and faced the girls, but kept an arm around Dean, “What’s in it for us if we do that?” Okay, Sam’s confidence was back full force. 

 _Oh two can play this game, Sammy._ Dean thought as he finally processed what was happening, he couldn’t be sure if Sam’s motives were to throw Dean off his game, get Dean to leave entirely, or just give the girls what they want.  And he had the gall to accuse Dean of trying to be an asshole not even five minutes earlier! Since they didn’t pre-negotiate anything other than ‘don’t be an asshole’ and ‘whatever the girls want to do,’ Dean was free to retaliate. He knew more than a few of Sam’s likes and dislikes about sex, even if he had to tease and pry the details out of him.  He had to be quick about it before Sam could counter.  He simultaneously turned toward Sam, grabbed a fistful of his hair, and jerked Sam towards him hard.  He crashed their mouths together, it wasn’t a kiss it was the same physical fight they always would get into.  Just a small detail that this fight involved their mouths, or that’s what he told himself.  His free hand dug into the meaty part of Sam’s ass through his jeans and he twisted his hand in Sam’s hair, between their clash of teeth and tongues Dean heard a small whimper. Sam shouldn’t have ever disclosed that he liked being treated rough.  _Revenge, fucker._ But Sam always did think quickly on his feet.  Sam snaked his hands between them and tweaked Dean’s nipples hard.  The jolt that went through Dean was immediate.  He pulled away, “Son of a bitch…” slipping out as he panted to catch his breath.  So much for getting Sam back. 

This was going to get more out of hand quickly if someone didn’t take control.  Instead of waiting for a response, Dean stalked over to the other side of the bed and grabbed Amy.  The redhead gasped as he quickly rolled her to her back, then jerked her to the edge of the bed by her hips.  Her legs were dangling over the side and she was slightly propped up on her elbows. He purposely leered over her, “Now, we were in the middle of something before some rude guy interrupted us.” He punctuated it with a quick kiss before he shoved her legs apart wide. He raised an eyebrow and looked at the other girl, “You don’t mind if I go back to that?” He leaned back and went for his belt buckle.  Sam was on the same page, already working on getting his jeans off too. 

Sam didn’t have the element of surprise on his side; his girl was looking back at him when he approached the bed. She leaned up to palm his erection through his boxer briefs.  Sam spoke to her, but loud enough that the other two could hear, “You gonna let me go back to getting that ass ready for me?” Tara moaned in response, and Dean bit his lip.  He didn’t say anything though.  Sam continued, “Turn over for me.” He grabbed the vibrator and the lube off the bed and put them on the nightstand. 

Dean had to comment, “Using a vibrator? Come on, man, that’s cheating!” 

Sam snapped his gaze up to Dean on the other side of the bed. “I found it so I got to use it.  It’s a rule, you know.” Dean should know.  He’s the one that taught Sam these alleged ‘rules.’ 

Dean chuckled in response, “It is.” He dropped his jeans and boxers in one swoop and knelt on the floor.  He resumed his previous path, kissing and licking up the insides of her thighs, but with more speed and urgency. This was no longer a night to take a girl apart.  This was a contest over who can make a girl come first, hardest, best.  And he was going to win all three.  She wasn’t expecting it when he latched onto her clit and plunged two fingers into her at the same time.  She was expecting him to go slow like before, the shock and pleasure had her eyes rolling back as she grabbed at the back of his head. It was a dirty trick, and Dean knew it, but he knew exactly how to make a girl squirt then orgasm hard in just under two minutes.  He didn’t bust it out often because the girl usually complains that they need a break afterwards.  Sam wasn’t as concerned about that, he already gave two orgasms to this girl and he was going to make her beg for the next one, Dean there or not, he still had his original mission.  Dean crooked his fingers inside the girl as he placed a palm firmly on her stomach. He continued sucking and flicking his tongue over her clit as he pressed his fingertips relentlessly over her g-spot.  His mouth was flooded with her tangy taste and he stepped up his efforts, leaning back and focusing on his hand inside her.  The squelching sound and her increasingly loud moans were filling the room. She grabbed his arm hard, “Wait… Don’t want to…” panting and trying to fight back the inevitable. 

“Don’t want to what, sweetheart? Don’t want to come on my hand? Why?” He leaned up, never stopping his movements, “You’ll look gorgeous.” He was used to that too, girls getting self conscious about this part. Hell, they do that when he’s alone with them, much less when there’s an audience and outside of her own bedroom. He could talk her through this, “Please,” he sped up, “Let me do this for you.” That was it, she was nodding yes and clenching pretty hard around him.  He leaned back between her legs for the show.  If he was honest, it’s a dirty trick but he loves the reaction.  She was arching up, “Dean!” and a large gush covered Dean’s hand and forearm. He kept going, knowing full well that squirting and orgasming is not the same thing, he fucked his fingers into her hard.  A few thrusts and her legs were quaking, she grabbed his arm hard enough that her nails dug in, and she was gone.  He leaned up, changing the angle, and finger-fucked her through it as her whole body shook. He pulled his hand away and watched her continue convulse involuntarily, he sucked his fingers into his mouth as he rummaged into his discarded jeans for a condom.  He gave his dick a few firm stroked, spreading what was left of her juices on him, before ripping open the condom wrapper and rolling it on. 

While Dean was busy over-stimulating his girl, Sam got Tara to roll over onto her hands and knees.  He placed a firm hand on her back between her shoulders to get her to drop her face and chest to the mattress, his other hand pulled her hips back and up higher.  He draped over her and leaned his face into her ear, “Stay.” He grabbed the bottle of lube again and coated three of his fingers with a generous amount. He circled her hole with one finger while his other hand was running up and down her leg, occasionally skimming across her ass.  He would push a finger in just to the first knuckle and withdraw it quickly, going back to circling and teasing around the rim.  After repeating this a few times she tried to push back onto his fingers, earning her a firm slap on the ass, “Be patient.” It was a warning but she took it as a challenge, “Hurry up!” A second slap followed and she yelped but Sam was pretty sure there was a moan in there.  Clearly she’s used to being in charge and not being challenged.  

He resumed his teasing, now pressing two fingers in to the first knuckle and withdrawing them.  He ghosted his other hand over the area between her holes and pressed slightly, that’s when she broke, “Please!” Sam let himself grin and did it again, harder, then lightly swatted a few times.  “Please please please Saaaaaaam,” that’ll do. He pushed two fingers in as far as they could go and began scissoring them; the moan that she let out was a good indication that she was happy with the results.  She could feel him stretching her and let out a startled yelp when she felt him drizzling more lube between his spread fingers into her.  He worked a third finger in, beginning to lose patience he changed the angle slightly to rub her sweet spot through her walls.  After she started writhing under him, Sam was satisfied that he had done a thorough job with the prep.  He withdrew his hand and wiped the excess lube off on his boxers before yanking them down. He grabbed the condom from his jeans and rolled it on.  He put more lube on and had lined up behind her when she spoke up. “Wait… wait,” she panted and Sam stopped.  He sincerely hoped he hadn’t done something wrong.  “Get them to come to this side of the bed. Wanna watch them.” 

Sam felt the air punch out of him.  The thought hadn’t crossed his mind, but watching Dean fuck a girl while he was also balls deep in a different girl, that was so filthy, wrong, decadent, and perfect… Dean heard too, and immediately locked eyes with Sam.  The look conveyed that they were on the same page and Sam stepped back and flipped Tara over wrapping her legs around his waist while Dean walked around to stand next to him. 

Under normal circumstances Dean wouldn’t have talked to another dude in a group sex situation, but under other circumstances he wouldn’t be doing this with his brother. “This how you’re staying?” Sam shrugged, he hadn’t really thought that far ahead.  Dean sat on the bed, extremely close to Tara, and tapped Amy on the leg, “Up.  I want you to ride me.” It was the gentlemanly thing to do, let her have control for a little bit. 

Amy straddled Dean with her knee close enough to Sam’s hand that he would probably be brushing against her every time he thrust. This was either a terrible idea or an amazing one. 

Sam gripped the base of his dick as he pushed into Tara, she was already arching up from all the teasing he’d done earlier. As he predicted, when he moved his hand to Tara’s hip to brace himself, he was brushing his knuckles along Amy’s leg.  The whole situation added a thrilling zing of arousal to what he was doing.  

Once Amy was braced over Dean she rocked back a few times, rubbing her pussy along his aching erection, just to get back at him for his earlier acts.  He immediately let one hand go to her ass to rub along the smooth, soft skin, while the other went behind his head.  He didn’t want to accidentally be caressing his brother during this.  After this it all became a blur.  Amy sank down on Dean’s cock but was brushing against Sam and Tara as she bounced and gyrated.  Sam was holding a brutal pace of thrusting into Tara, but both ended up touching Dean or Amy as his thrusts kept moving her up the bed. 

Tara was clearly enjoying what Sam was doing to her but was more focused on watching the other two.  Sam would be lying if he denied looking over and loving it. Sam wasn’t expecting this change in position meaning that he’d be looking at Dean’s face.  And he couldn’t stop looking either. Dean really did look incredible as he parted his lips to pant and moan…. Woah, maybe stop that thought right now… 

Dean was thrusting up to meet Amy’s pace, but seeing Sam and his merciless pace with Tara was becoming overwhelming. He finally spoke up when he locked eyes with Amy, “Stop, stop.  Want you on my face….” When she didn’t stop, he gripped her hips hard and repeated, “Sit on my face.” And who could deny a request like that? After she got off him, he added, “You can face them if you want,” with a naughty smile that implied he would appreciate it if she did.  So she ended up straddling his head, facing Sam as he thrust into her friend. The whole sight was overwhelming. Then Dean started in with his tongue.  She nearly lost it again. 

Sam saw this as an opportunity.  As overwhelmed as he was by the situation, it was still an opportunity for bragging rights over Dean.  So with Dean’s vision blocked and his attention occupied, Sam took action.  He could tell Amy was occupied with holding off her next orgasm, just to make Dean work harder for it.  So he grabbed Tara’s hand, without letting up his own pace, and brought it to Dean’s cock. He wrapped her fingers around it and she got the hint, jacking Dean at the same pace that Sam was fucking into her.  It didn’t take long before Dean was practically throwing the poor girl off his face to bat away the hand, “Enough enough enough, shit…” He was seconds from blowing his load and had to grip the base of his erection like a vice to keep from coming. Sam took way more satisfaction in that than he should have. 

Dean got up off the bed and stood next to Sam, flipping Amy and bringing her to her hands and knees.  He knew he wasn’t going to last much longer and wanted to go with a position he knew he had success with most of the time. He planted one foot on the bed and started pistoning his hips at a downward angle.  She didn’t stand a chance.  Even when he heard her scream, felt the tight grip and warm gush of fluid, he kept going.  He kept going until she was practically forcing him off with her arm pushed back awkwardly against his chest.  “You done?” he asked with a cocky grin.  “Yeah,” was her fucked out, breathless response. 

She turned and gripped his cock, getting ready to suck him off.  She went to pull the condom off when he batted her hand away, “It stays on.” He was firm enough to let he know there wasn’t room for negotiation in it.  Dean had it hammered into his head that you’re to be careful with where your body fluids end up – too much bad hoodoo that can come back on you if you don’t.  At this point it was a neurotic habit.  That didn’t mean he couldn’t stand there and enjoy a hot woman sucking him off while he wore a condom.  She was doing it like a champ, and Sam was still keeping his unfaltering pace with his girl.  Dean didn’t last long, and didn’t see a need to hold out at this point.  After a respectable amount of time with Amy sucking him off, he came with a hand in her hair and other gripping her shoulder. 

When he came down he could still see Sam keeping pace. This wouldn’t do. He was done and Sam needed to be done too, he wasn’t walking back to the motel alone! This also presented a second opportunity to get back at Sam, finally.  Amy was really and truly done for the night, as she lay boneless on the bed.  So Dean sidled close to Sam and started with his plan.  He locked eyes with Tara and started speaking, “I can’t believe you don’t have your fingers inside yourself right now.  Bet he’s got you filled so much that you could barely fit them in…” Sam lost his rhythm and grunted loudly, “Shut the fuck up, Dean!” Sam was also a sucker for filthy, dirty talk in bed.  Another fun fact Dean knew and used to his advantage. 

Dean took it a step further, grabbing one of Tara’s hands and leading it between her legs, his hand was bumping into Sam’s stomach as he continued his thrusting.  He took two of her fingers and lined them up with her entrance. When she didn’t act immediately, he pushed them in along with one of his own.  If he hadn’t already come earlier, he would’ve lost it now. She was incredibly tight and he could feel the ridges of Sam’s dick as he thrust it in and out. He decided to go for the kill… he pulled his hand away and got behind Sam.  “So good, you’re fucking her so hard,” he spoke as he slid his hands over Sam’s chest.  Echoing Sam’s actions from earlier, he gripped both nipples and twisted as he intentionally sank his teeth into Sam’s shoulder.  And just like that Sam was coming like a freight train. His knees actually buckled, he would have fallen backwards if Dean wasn’t standing right there. Sam leaned forward and braced his hands on he edge of the bed, “You fucking asshole,” he managed to get out as he panted in his aftershocks.  

By the time Sam composed himself long enough to stand properly, Dean was already in his jeans with boots on. He was looking for his shirt and jacket when Sam started dressing.  Both were dressed rather efficiently and left after the customary, awkward goodbye after a good one night stand. 

It would be a good twenty or twenty-five minute walk to the motel from here.  They walked in silence for several minutes before Dean finally broke the silence, “That was…” 

“Yeah,” Sam agreed before Dean even finished the sentence.  After thirty seconds of silence Sam spoke up, “You’re a jerk by the way, did you really need to do that shit at the end?” 

Dean laughed, “No, bitch, but I didn’t want to do this walk by myself, and I don’t have stamina like I used to.” 

Sam rolled his eyes and bashfully admitted, “… It was fun though.” 

Dean practically lit up, “Oh, we’re definitely doing that again Sammy!”

**Notes for the Chapter:**

> I should probably apologize for this but I'm not sorry. Kudos and comments appreciated.

**Author's Note:**

> I wrote this after the wonderful positive feedback for my first fic "I Like To Watch." Comments and kudos are greatly appreciated.


End file.
